CHEMISTRY OF DENUDATINE .5. REARRANGEMENT REACTIONS OF DENUDATINE

Authors
WANG FP WANG JZ ZHANG R
Citation
Fp. Wang et al., CHEMISTRY OF DENUDATINE .5. REARRANGEMENT REACTIONS OF DENUDATINE, Heterocycles, 45(4), 1997, pp. 659-672
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
4
Year of publication
1997
Pages
659 - 672
Database
ISI
SICI code
0385-5414(1997)45:4<659:COD.RR>2.0.ZU;2-T
Abstract
Treatment of denudatine 1 with 10% HCl solution at 30-50 degrees C lea ds to rearrangement to two pairs of epimers (5A) and (5B), (8A) and (8 B) as well as 7 and 15. The rearrangement mechanisms are discussed. Co nversion of 7-->5A/5B-->15 under acid catalysis can be realized. While the conversion of 15 to 5A/5B can be realized with NaOH-DMF at 120-12 6 degrees C. Structures for 5A/5B, 7, 8A/8B and 15 were established on the basis of chemical and spectral methods.